3-Chloro-4-(2-diethylaminoethoxy)phenylamine → HCID 57845845, compound

HRID 1820870Notes

Reaction equation

HRID 1820870 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:9](Cl)=[O:10])=[CH:3][CH:2]=1.[Cl:18][C:19]1[CH:32]=[C:31]([NH2:33])[CH:30]=[CH:29][C:20]=1[O:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:18][C:19]1[CH:32]=[C:31]([NH:33][C:9](=[O:10])[C:8]#[C:7][C:4]2[CH:5]=[CH:6][C:1]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:2][CH:3]=2)[CH:30]=[CH:29][C:20]=1[O:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamineHCID 86070401Biphenyl-4-ylpropynoic acid chloride

Product 1

HCID 57845845HCID 57845845, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

0.48 g (2.0 mmol) of biphenyl-4-ylpropynoic acid chloride (for preparation method see Bioorg. Med. Chem. 1996, 4, 851) is dissolved in 15 mL of toluene and 0.58 g (2.4 mmol) of [2-(2-chloro-4-aminophenoxy)ethyl]diethylamine (educt IV.1) in 10 mL of toluene at ambient temperature is added dropwise. The mixture is stirred for 8 hours at ambient temperature, the solvent is eliminated, and the residue is taken up in ethyl acetate and washed with water. The organic phase is dried over sodium sulfate, the solvent is eliminated and the residue is purified through a silica gel column with dichloromethane/methanol/ammonia (9:1:0.01) as eluant. Yield: 0.28 g (31% of theory); m.p.: 105-108° C.; Rf value: 0.50 (silica gel, dichloromethane/methanol/ammonia=9:1:0.1); C27H27ClN2O2; EII mass spectrum: m/z=447/449 [M+H]+.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customthe residue is purified through a silica gel column with dichloromethane/methanol/ammonia (9:1:0.01) as eluant

Sources & evidence

ORD record
ord-b990486a63b94e6d8761f338cb8d3e02
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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